Matt Singley – Founder & CEO, Pinnacle Furnished Suites

Matt Singley is a graduate of Bradley University with a Bachelor’s degree in Mechanical Engineering. After a short career as a project manager working in nuclear power plants throughout the southern US, his entrepreneurial drive took over and he “retired” from his first job to start Pinnacle Furnished Suites and various other smaller companies. He currently calls the West Loop of Chicago home.

How did the concept for Pinnacle Furnished Suites come about?
After graduating college, I began my career as a mechanical engineer working on projects at nuclear power stations across the Southern US. During the very early years, there were slow periods at work (working only 40 hours) where I had some extra time to research topics that interested me outside of my field. One of these topics was real estate. I had a friend, Collin Walker, who had started his own brokerage around that time, and I found myself discussing real estate opportunities with him quite regularly. Through a series of distressed property acquisitions in 2009 and 2010, we became quite close and noticed an industry called “corporate housing.” Collin, being very in tune with apartment pricing throughout Chicago, approached me with an idea to furnish an apartment and rent it out on a short-term basis. We had heard through the grapevine what similar companies were charging for something like this and thought it would be a great way to use our relationships and resources to fill a need. The margins were there, and we figured we could do it significantly cheaper and find enough clients to keep us in the black. A short time later, that single apartment turned into 10, then 20, then 30, all while maintaining literally zero vacancies. It was evident we had something here.

How was the first year in business?
The first year in business was absolutely grueling. Collin was running the brokerage full-time, and I was advancing in my engineering career. I was running a team, traveling constantly, and heavily involved in business development throughout Louisiana and Arkansas. With all this, however, our new business, Pinnacle Furnished Suites, continued to grow. I was working 50+ hours at the day job and working another 30 attempting to keep up with the demands of the new enterprise. Lunch hours were spent sprinting to apartment buildings, setting up units, meeting clients, and trying to keep the ship straight. Bathroom breaks and elevator rides were spent furiously sending off emails and text messages. Early mornings and evenings were spent answering emails, marketing, developing the website, and attempting to standardize processes. A full night’s sleep was a luxury I could no longer afford. I still didn’t know which route my life would take, so I had to keep both options fully open. Right around the 1-year mark, it became evident I needed to make a decision. I decided to “retire” from engineering and go “all in.” I ended up consulting for my old company for another year (a few hours a week) to keep what I had built there going and transition smoothly. Honestly, it was a tremendous opportunity and a privilege to be afforded that transition period. It allowed me to be confident in what I had built and left, but still transition into what would become my new passion.

What was your marketing strategy?
Somewhat amazingly, PFSuites built off the success the brokerage had utilizing Craigslist for advertising. Early on, we knew the trend in real estate was moving towards full disclosure, great pictures, and truly showcasing what you had. Many competitors used generic photos and general descriptions, while we professionally-photographed every single building and unit to truly give our clients a feel for what they were moving into prior to signing with us. I had a good friend from college, John Moats, who did website design, and we utilized his services early on to build a full, modern website in an industry that typically relied on decades-old relationships and partners, as opposed to digital marketing. This turned out to be a crucial decision which transitioned into a full-blown property management software and “company brain.”

The combination of lower pricing, Craigslist, and a superior digital marketing platform allowed us to gain significant market share in the early days. Our focus on business-to-client contracts, as opposed to business-to-business, turned out to be a decision which caught the trend before it began and took hold. AirBnB, HomeAway, and VRBO were just becoming popular and even C-level execs were starting to realize they wanted to control the process and pick their own properties. Our platform and approach were perfectly-aligned with this trend, which continues to grow to this day.

How fast did the company grow during the first few years?
PFSuites started in 2014 as a side project with a small number of units from trusted property managers we knew from the residential side of the business. We operated in three buildings with just a few units in each building. The first year’s sales were moderately above six figures, but profit margins were through the roof! Having no overhead really makes you think you’re on to something.

In 2015, things really started to pick up and we realized this was no longer a project, but a full-fledged business. We hired our first employees that summer and started to expand our risk profile, wanting to take advantage of a strong economy and what we saw as a tremendous opportunity. Year-over-Year (YoY) revenue growth was over 1000% that year!

2016 saw YoY revenue growth of 107% and the hiring of even more support staff. Another blockbuster year!

2017 experienced 22% YoY revenue growth.

In 2018, PFS was awarded the position of No. 159 on the Inc. 5000 list of fastest-growing private companies with a 3-year growth rate of 2669%. The 2018, YoY revenue growth clocked in at 19.7% and contained a geographical expansion into Nashville corporate housing.

How do you define success?
There are various ways to “measure” success when it comes to business. How much money do you make? How big of an impact do you have? How much do you grow? These are all important indicators, but they boil down to noise. Of course, you need to be profitable to stay in business, but it doesn’t “define” success.

To me, success can be described as the feeling I get when a team member thanks me for what we’ve been able to do for them and their family, or the look on someone’s face when you give them new benefits or a nice (and well-deserved) raise. The feeling of comradery and what the team member would do for me and for each other truly takes my breath away sometimes. Creating something that can provide for not only myself but also a growing group of people truly makes me feel successful. I only hope we can continue to grow the family we have all come to know and love over the past few years. I would truly retire a happy and complete man.

What is the key to success?
This plays into the last question on how you define success, but there is more to it. The end-result might be how you define it, but the key to it is a much more complicated question. Obviously, I could focus on the usual “You must love what you do and believe in it” mantra, but everyone says that. It’s true, but it’s more than that.

The true keys to becoming successful, from a business perspective, are to work your butt off and never stop. Ever, especially in the early years. I can’t tell you how many times I’ve worked 16 (or longer) hour days, 5 days in a row. I can’t begin to explain the vacations I’ve canceled or family events I’ve interrupted with phone calls. I wake up multiple times throughout the night and check/respond to emails. It’s, honestly, crazy. There are those who question whether those decisions are worth it, and at times I’ve wondered myself, but I always come back to those feelings I have when others share in our success. It makes it all worth it, and it won’t always be like this. I don’t think…

What is the greatest lesson you’ve ever learned?
My parents have taught me many great lessons and have given me loads of advice, some of which I heeded, and some of which I ignored. One of the greatest lessons I was taught, however, was to always maintain a sense of humor and a positive attitude. There will always be things that happen outside of your control that really, truly, suck. What you do have control over, however, is your attitude and reactions following those bouts of frustration. Even in the worst of times, arguments, or periods of sadness, my father was somehow always able to crack a joke and make me smile. He has an amazing ability to conjure humor from almost anywhere, and I think this attitude has carried on to me in some capacity. There are times in business where you must have very serious, and sometimes very stressful, conversations with clients and employees. I’ve found that having the ability to laugh, even in these times, helps you get through them with a positive attitude and a desire to “push on.” The greatest lesson I’ve ever learned is to never be so mad or upset that you can’t recognize the potential humor in a situation and use that to get through it.

What are some quotes that you live by?
I’m not really a “quote guy,” but I always liked “Line ’em up and knock ’em down” as a reference to all the obstacles that come at you in a given day. All you can do is set ’em all up and tackle them.

What advice would you give to young entrepreneurs?
This advice might seem a little contrary to what you might hear on Shark Tank and from some other entrepreneurs, but it’s important to understand the nuances in what I’m saying. Others will tell you, “Dive in and give it your all, or don’t bother trying at all.” I don’t believe this to be the catch-all phrase that some claim it is. Maybe it’s just my personal experience, and luck, that led me to where I am today, but there’s something to be said for “tip-toeing” or “wading” into a new venture or business, as opposed to diving in. I was fortunate enough to have a career and a well-paying job while we started this new company, and I continue to have that benefit as I start various other new companies. I believe that having this financial support system or fail-safe while you try riskier possibilities can be paramount to success. You always have more time to devote to something you believe in. Sometimes, starting something on the side and gauging how it’s working can provide the stability you need to really get it off the ground.

Don’t get me wrong, there becomes a point where you have to “pull the trigger” and waiting beyond that point can be detrimental. Find the balance while you create your foundation. At that point, however, don’t be afraid to jump in and swim with the sharks.



This interview was conducted for research purposes by Jason Navallo for his upcoming book, Underdog.

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